Journal of Organic Chemistry, volume 87, issue 5, pages 2456-2469
P2O5-Promoted Cyclization of Di[aryl(hetaryl)methyl] Malonic Acids as a Pathway to Fused Spiro[4.4]nonane-1,6-Diones
Ivanov Konstantin S
1
,
Riesebeck Tim
1
,
Skolyapova Alexandrina
1
,
Liakisheva Irina
1
,
Kazantsev Maxim S.
1, 2
,
Beloborodova Alina
1, 2
,
Peshkov Roman Yu
1
,
Publication type: Journal Article
Publication date: 2022-02-15
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
Conventional spiro-linked conjugated materials are attractive for organic optoelectronic applications due to the unique combination of their optical and electronic properties. However, spiro-linked conjugated materials with conjugation extension directed along the main axis of the molecule are still only rare examples among the vast number of spiro-linked conjugated materials. Herein, the synthesis, leading to π-extended spiro-linked conjugated materials─spiro[4.4]nonane-1,6-diones and spiro[5.5]undecane-1,7-diones─has been developed and optimized. The proposed design concept starts from readily available malonic esters and contains several steps: double alkylation of malonic ester with bromomethylaryl(hetaryl)s; conversion of a malonic ester into the corresponding malonic acid; electrophilic spirocyclization of the latter into the annulated spiro[4.4]nonane-1,6-dione or spiro[5.5]undecane-1,7-dione in the presence of phosphorus pentoxide. On the basis of these insights, the developed method yielded spiro-linked conjugated cores fused with benzene, thiophene, and naphthalene, decorated with active halogen atoms. The structures of the synthesized spirocycles were determined by single-crystal X-ray diffraction analysis. Benzene fused spiro[4.4]nonane-1,6-dione decorated with bromine atoms was transformed into V-shape phenylene-thiophene co-oligomer type spirodimers via Stille coupling. The spiro-bis(4-n-dodecylphenyl)-2,2'-bithiophene derivative possessed high photoluminescence properties in both solution and solid state with a photoluminescence quantum yield (PL QY) of 38%.
Citations by journals
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1
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Journal of Organic Chemistry
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Journal of Organic Chemistry
1 publication, 25%
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Progress in Heterocyclic Chemistry
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Progress in Heterocyclic Chemistry
1 publication, 25%
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European Journal of Organic Chemistry
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European Journal of Organic Chemistry
1 publication, 25%
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Tetrahedron Letters
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Tetrahedron Letters
1 publication, 25%
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1
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Citations by publishers
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1
2
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Elsevier
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Elsevier
2 publications, 50%
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American Chemical Society (ACS)
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American Chemical Society (ACS)
1 publication, 25%
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Wiley
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Wiley
1 publication, 25%
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1
2
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- We do not take into account publications that without a DOI.
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- Statistics recalculated weekly.
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Ivanov K. S. et al. P2O5-Promoted Cyclization of Di[aryl(hetaryl)methyl] Malonic Acids as a Pathway to Fused Spiro[4.4]nonane-1,6-Diones // Journal of Organic Chemistry. 2022. Vol. 87. No. 5. pp. 2456-2469.
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Ivanov K. S., Riesebeck T., Skolyapova A., Liakisheva I., Kazantsev M. S., Beloborodova A., Peshkov R. Yu., Mostovich E. A. P2O5-Promoted Cyclization of Di[aryl(hetaryl)methyl] Malonic Acids as a Pathway to Fused Spiro[4.4]nonane-1,6-Diones // Journal of Organic Chemistry. 2022. Vol. 87. No. 5. pp. 2456-2469.
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TY - JOUR
DO - 10.1021/acs.joc.1c02379
UR - https://doi.org/10.1021%2Facs.joc.1c02379
TI - P2O5-Promoted Cyclization of Di[aryl(hetaryl)methyl] Malonic Acids as a Pathway to Fused Spiro[4.4]nonane-1,6-Diones
T2 - Journal of Organic Chemistry
AU - Ivanov, Konstantin S
AU - Riesebeck, Tim
AU - Skolyapova, Alexandrina
AU - Liakisheva, Irina
AU - Kazantsev, Maxim S.
AU - Beloborodova, Alina
AU - Peshkov, Roman Yu
AU - Mostovich, Evgeny A.
PY - 2022
DA - 2022/02/15 00:00:00
PB - American Chemical Society (ACS)
SP - 2456-2469
IS - 5
VL - 87
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2022_Ivanov,
author = {Konstantin S Ivanov and Tim Riesebeck and Alexandrina Skolyapova and Irina Liakisheva and Maxim S. Kazantsev and Alina Beloborodova and Roman Yu Peshkov and Evgeny A. Mostovich},
title = {P2O5-Promoted Cyclization of Di[aryl(hetaryl)methyl] Malonic Acids as a Pathway to Fused Spiro[4.4]nonane-1,6-Diones},
journal = {Journal of Organic Chemistry},
year = {2022},
volume = {87},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021%2Facs.joc.1c02379},
number = {5},
pages = {2456--2469},
doi = {10.1021/acs.joc.1c02379}
}
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Ivanov, Konstantin S., et al. “P2O5-Promoted Cyclization of Di[aryl(hetaryl)methyl] Malonic Acids as a Pathway to Fused Spiro[4.4]nonane-1,6-Diones.” Journal of Organic Chemistry, vol. 87, no. 5, Feb. 2022, pp. 2456-2469. https://doi.org/10.1021%2Facs.joc.1c02379.
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